I think I was only 10-12 when I played Red Rescue Team. I recall feeling sad when my Pokemon was going to leave, but I didn't cry.

Now Explorers of Sky. This was in August 2012 that I finished it. I got sad, got the feeling in my throat like when I'm about to cry.. So I held my breath for about 10 seconds. Then I burst out, weeping very, very loudly as I continued through the ending of the game, I remember my DS was soaked.
However, I think a lot of my crying was a release of frustration and stress, not just being sad about the game. I try to keep myself from crying, but once the faucet is on.. Well, it's on full blast.

I was also really upset and confused on how my character was allowed to come back and Grovyle wasn't. And honestly, in my mind Grovyle and the others do still exist, just in a different future, with no recollection of the other future. And my character had gone to that future when she "ceased to exist" and was just re-put on the current world with her old memories. Yep, that's my story and I'm sticking to it. But seriously, I barely played past the main story because I was so confused and upset.